Electrochemical Direct Synthesis of N-Sulfenylimines from Amines in the Presence of Thiophenols.

N-Sulfenylimines are important molecules owing to their value in organic synthesis. Herein, we developed an electrochemical oxidative cross-coupling reaction between amines and thiols to synthesize N-sulfenylimines without a transition-metal catalyst and external oxidant. Various amines and thiols were compatible, generating the desired products in up to 86% yield.

Chiral Phosphoric Acid-Catalyzed Enantioselective Reductive Amination of 2-Pyridyl Ketones: Construction of Structurally Chiral Pyridine-Based Ligands.

A chiral phosphoric acid-catalyzed one-pot enantioselective reductive amination of 2-pyridyl ketones was realized to provide chiral pyridine-based ligands in excellent yields with high enantioselectivities (up to 98% yield, 94% ee). Computational studies on the key intermediate imine and transition state of the hydride transfer process revealed that the nitrogen atom of the pyridyl ring might be an important factor to significantly promote both the reaction activity and enantioselectivity.